Cheap flights from Toronto to Chicago

Depart
Return
Any month
Compare vs. momondo |

Toronto to Chicago flight comparison made easy

Below you can see the best fares for your route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Toronto to Chicago by changing tabs
Quickest
Cheapest
Porter Airlines
Porter Airlines
31 Oct.
YTZ
9:00 a.m.
Toronto Island airport
1h 47m
9:47 a.m.
MDW
Chicago Midway airport
Porter Airlines
07 Nov.
MDW
1:00 a.m.
Chicago Midway airport
1h 42m
3:42 a.m.
YTZ
Toronto Island airport
263 CAD
Porter Airlines
Porter Airlines
01 Nov.
YTZ
9:00 a.m.
Toronto Island airport
1h 47m
9:47 a.m.
MDW
Chicago Midway airport
Porter Airlines
07 Nov.
MDW
1:20 p.m.
Chicago Midway airport
1h 42m
4:02 p.m.
YTZ
Toronto Island airport
263 CAD
Porter Airlines
Porter Airlines
02 Nov.
YTZ
10:45 a.m.
Toronto Island airport
1h 47m
11:32 a.m.
MDW
Chicago Midway airport
Porter Airlines
07 Nov.
MDW
5:57 a.m.
Chicago Midway airport
1h 42m
8:39 a.m.
YTZ
Toronto Island airport
263 CAD
United Airlines
United Airlines
14 Oct.
YYZ
4:16 a.m.
Toronto Pearson Intl airport
1h 47m
5:03 a.m.
ORD
Chicago O'Hare Intl airport
United Airlines
15 Oct.
ORD
1:00 a.m.
Chicago O'Hare Intl airport
1h 36m
3:36 a.m.
YYZ
Toronto Pearson Intl airport
324 CAD
Air Canada
Air Canada
24 Oct.
YYZ
10:55 a.m.
Toronto Pearson Intl airport
1h 49m
11:44 a.m.
ORD
Chicago O'Hare Intl airport
Air Canada
29 Oct.
ORD
3:35 p.m.
Chicago O'Hare Intl airport
1h 35m
6:10 p.m.
YYZ
Toronto Pearson Intl airport
324 CAD
Air Canada
Air Canada
25 Oct.
YYZ
4:55 p.m.
Toronto Pearson Intl airport
1h 49m
5:44 p.m.
ORD
Chicago O'Hare Intl airport
Air Canada
29 Oct.
ORD
4:25 a.m.
Chicago O'Hare Intl airport
1h 36m
7:01 a.m.
YYZ
Toronto Pearson Intl airport
324 CAD

How to get the cheapest flight from Toronto to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight for your trip
What is the cheapest month to fly to Chicago?
February
The cheapest time of year to fly to Chicago from Toronto is February. The most expensive is August.
What is the cheapest day to fly to Chicago?
Wednesday
The cheapest day of the week is typically Wednesday. The most expensive is typically Sunday
When is the cheapest time to fly to Chicago?
at noon
Toronto to Chicago flights are approximately 10% more expensive in the evening than at noon
What is the cheapest airline that flies to Chicago?
Porter Airlines
Porter Airlines, Air Canada, and Iberia are the most popular carriers operating from Toronto to Chicago
What is the cheapest route?
Toronto Island - Chicago Midway
Fly from Toronto Island to Chicago Midway for the best Toronto - Chicago flight prices
When is the cheapest time to book a flight to Chicago?
60 days before
The cheapest time to buy a flight from Toronto to Chicago is approximately 60 days before departure
60
Days before departure
0

Flight information for Toronto to Chicago

Find info about flight duration, direct flights, and airports for your flight from Toronto to Chicago
Fastest flight time 1h 45m The fastest flight from Toronto to Chicago takes 1h 45m.
Direct flights Every day Direct flights go from Toronto to Chicago every day.
Airports in Chicago 3 airports There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

Alternative routes for Toronto to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Toronto to Indianapolis
Fastest flight time
1h 39m
Cheapest price
482 CAD
Kingston to Chicago
Fastest flight time
4h 10m
Cheapest price
504 CAD
Toronto to Champaign
Fastest flight time
6h 59m
Cheapest price
653 CAD

Flights from Toronto to:

Flights to Chicago from: